How Whitey Bulger Bought Boston

The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century, Howie Carr, Warner Books, 342 pages

by William Norman Grigg | June 23, 2011

Peggy Westcoat was a woman of small skills and modest ambitions. Just before Christmas in 1980, two men broke into the single-family home Peggy shared with a live-in boyfriend in southwest Dade County. The intruders threw a rope around the boyfriend’s neck and hanged him near the front door. They then grabbed Peggy, shoved her against the kitchen sink, draped a noose around her neck, and began feeding the other end of the rope into a garbage disposal.

With the rope tight enough to terrify the victim without rendering her unconscious, the assailants turned off the grinder and began asking the terrified woman about her work as a cashier at the Miami “fronton” (or arena) of World Jai Alai, an exotic Iberian sport that had been controlled by Bostonians since the 1920s. A few months earlier, World Jai Alai had been sold to a new owner, and Boston’s Winter Hill mob—led by James “Whitey” Bulger—wanted to know if the new owners had discovered the mob’s skimming operation. Satisfied by Peggy’s panicked answers, the invaders flipped the switch on the disposal.

“When the cops found the two bodies the next day,” notes Boston Herald columnist Howie Carr in The Brothers Bulger, “they chalked it up as another Miami drug deal gone bad.” In fact, it was just one of scores of murders committed by a Boston crime combine that wedded the Irish mob to the FBI. That marriage eventually broke up in 1996, when Bulger—tipped off by his FBI handler, John Connolly—fled the United States one step ahead of several murder indictments. He is presently number two on the FBI’s Most Wanted list, below another one-time asset of the federal government named Osama bin Laden.

Connolly, convicted of various racketeering charges, is in prison until at least 2010. He also faces first-degree murder charges in Florida for allegedly providing information that led to the murder of Peggy Westcoat’s one-time boss, World Jai Alai president John Callahan.

At the time of Peggy Westcoat’s murder, the head of security for World Jai Alai was retired FBI Special Agent H. Paul Rico. Rico had taken note of Whitey Bulger in the early 1950s, when the future head of the Irish mob was a small-caliber hoodlum working as a homosexual prostitute. Rico, writes Carr, “could justify his sojourns to the Bay Village gay clubs as reaching out to new ‘sources.’”

From the very beginning of his career as a South Boston thug, Bulger was an informant. Gangsters planning to hijack a truck “might mention something about a future score to Whitey, just in passing, and sure enough, when they showed up to grab the truck, the FBI or the local cops would be there waiting,” Carr recounts. “H. Paul Rico’s personnel file soon included commendations from the director, J. Edgar Hoover. At the same time, no one suspected Whitey—it was inconceivable that one of Southie’s own would become a rat.”

Sent to prison in Atlanta for bank robbery in 1956, Whitey volunteered to serve as a test subject in LSD experiments in exchange for time off his 20-year sentence. “We were recruited by deception,” Bulger later complained, recalling that he was supposedly helping find “a cure for schizophrenia.” Dr. Jules Pfeiffer, who supervised the experiments, was working off a grant provided by the CIA, which probably wasn’t interested in humanitarian applications of the drug.

Whitey returned to Southie in 1965, just in time to benefit from three critical developments. First, the FBI—in keeping with Robert Kennedy’s priorities—had decided to tear into La Cosa Nostra (better known as the Mafia). Special Agent Rico thus began to cultivate informants and allies within the Winter Hill mob, the Mafia’s deadly rival.

Second, just days before Whitey’s return, one of Rico’s informants, Jimmy “The Bear” Flemmi, murdered an undistinguished thug named Edward Deegan. In order to protect their informant, the Boston FBI office conducted a cover-up, sending four admittedly unsavory men to prison for Deegan’s murder, which they didn’t commit. By collaborating in that murder and cover-up, the Boston FBI office effectively “made its bones” as a full-fledged ally of the Irish mob.

But for Whitey Bulger the most propitious development was the emergence of his younger brother Billy as a rising political star in Bay State politics, which Carr describes as seamlessly integrated with the underworld.

In 1961, when the Kennedy family entered the White House and Billy Bulger made his debut as a state legislator, the informal rules of conduct on Beacon Hill “boiled down to three points: Nothing on the level; everything is a deal; no deal [is] too small,” writes Carr. Massachusetts novelist Edwin O’Connor describes state politics as “a special kind of tainted, small-time fellowship” through which “even the sleaziest poolroom bookie managed, in some way, however obscure, to be in touch with the mayor’s office or the governor’s chair.”

Billy Bulger would eventually become president of the state Senate, a post that allowed him to dispense patronage as he saw fit. Boston-born FBI agents like Paul Rico, who confronted mandatory retirement at 50, were eager to cultivate Billy Bulger’s favor. By racking up arrests of Italian mobsters, the G-men could earn promotions and plaudits. By taking care of the Bulger family, they could supplement their federal paychecks and maybe arrange cushy post-retirement sinecures at Boston Edison or some other hack habitat.

Before leaving Boston for Miami in 1970, Rico recruited Steve Flemmi, a close associate of Whitey Bulger who was also tied in with the Italian mob, as a “top echelon informant.” Five years later, Whitey—who had by then established himself as a secure but unremarkable racketeer—was also granted “top echelon” status. Flemmi would scrape up intelligence on the Italians, and Whitey would pass it along to the feds. As Flemmi later described it, this relationship produced a perverse alchemy: “Me and Whitey gave [the Feds] sh-t, and they gave us gold.”

Why was Whitey included in this package deal, when Flemmi was the one with the mob contacts? As Carr points out, the Boston FBI office “didn’t need Whitey nearly as much as they needed his brother Billy”—and the favors that Billy could dispense on those who took care of his interests, including Whitey.

By 1980, Whitey, Stevie, and the FBI “were partners,” notes Carr. “And from the beginning, it was a one-sided deal. Each side would do ‘favors’ for the other, but the FBI’s were a lot more valuable than the cash and gifts that Whitey and Stevie would pass on to their agents.” Whitey and his handler, Special Agent Connolly, had grown up a few blocks apart from each other. They both wanted to take down Boston’s Italian mob—Connolly because doing so was the key to promotion within the bureau and Bulger because he wanted to clear the field of any rivals.

Connolly, who has tried unsuccessfully to sell a screenplay lionizing himself as the man who took down the Boston branch of the Mafia, has described his entente with Bulger as a brilliant “business” strategy—protecting one mob chieftain to take down scores of others. But that business arrangement was nothing less than a license for Bulger and his cronies to murder, extort, and rape with impunity. They also seized control over the local narcotics trade even as Bulger was heralded in the Boston Globe as a kind-hearted Robin Hood who was “keeping drugs out of Southie.”

In his own memoir, Brutal, one-time Bulger henchman Kevin Weeks observed of Whitey that while “nothing seemed to relax him or feel quite so good as a murder,” he was “calculating” and disciplined in killing. Flemmi, on the other hand, “would kill someone, anywhere, anytime.” Bulger and Flemmi were also incorrigible pederasts, the latter indulging a taste for underage girls, the former preying on children of both sexes.

Weeks also claims that Connolly and his corrupt fellow agents did more than merely look the other way. He asserts that Bulger “had six [agents] he could call on anytime and they would willingly hop in the car with him with the machine gun.” Being on the take was quite profitable for Connolly. A former secretary testifies that she once saw no fewer than ten uncashed federal paychecks in Connolly’s desk—a potent illustration of the contempt he felt for the substantial if unspectacular wages paid to an honest G-man.

While Connolly and his ilk were living large, honest Southies were living in terror. Carr and Weeks both describe the plight of Steve “Stippo” Rakes, a Southie who in 1983 scraped together enough money to buy a small piece of commercial property that he turned into a liquor store—the only one on Old Colony Avenue with convenient parking. As Rakes’s store began to prosper, anonymous death threats came spilling from his telephone. He soon fell prey to a Bulger protection racket and was forced to sell his business on concessionary terms. Renamed the South Boston Liquor Mart, the pilfered business soon became a favored hang-out of Bulger’s political allies.

During the 1987 Christmas season, relates Carr, “agents of the Boston FBI office bought the booze for the annual holiday party at the South Boston Liquor Mart. For the FBI the price was always right.” At John Connolly’s retirement party three years later, after the corrupted agent had heaped praise on Billy Bulger for getting him his job at the bureau and arranging his post-retirement gig at Boston Edison, he was handed a bottle of wine he was told came “courtesy of South Boston Liquors.” “No finer liquor store in the commonwealth,” replied Connolly with a knowing smirk.

What of Steve Rakes, who had that liquor store stolen from him by the FBI’s “top echelon informant”? Summoned to testify before two grand juries, Rakes—who had a wife and two daughters to protect—refused to talk. He was eventually convicted of perjury and sentenced to probation. Facing destitution, Rakes sought out a hack job with the Massachusetts Bay Transportation Authority. A friendly politician arranged one for him—in exchange for a $3,000 bribe.

“Absent justice,” wrote Augustine in The City of God, “what are kingdoms but vast robberies?” The unfathomably corrupt union of the criminal underworld and political “overworld” described by Carr offers a compelling illustration of what Augustine had in mind.

William Norman Grigg is the author of four books and Senior Editor of The New American magazine.

Makes you wonder how many federal and government financial agents have become rich on the bank and mortgage failures protecting all the banker types the past three years.

There have been a few arrests but nothing compared to the injustice perpetrated on the American people and future generations. We are having a falling from grace as we become a large bloated banana republic.

I’ve attacked Howie Carr on other issues–on war and foreign policy, he’s a neocon shill, and has otherwise become a Republican party publicist–but his courage in taking on the Bulger mob is beyond question. With maybe two or three exceptions (at best), everyone in the Massachusetts political and media establishment, and in a great many places outside of Massachusetts, on both the left and the right, either out of fear or trendy laziness, was in the pockets of the Bulger brothers for an entire generation–except for Howie Carr. He brought the issue to the forefront of Massachusetts politics, and kept it there, even as Bulger shills, in print, radio and other places, romanticized Billy & Whitey as a real-life, modern day “Angels With Dirty Faces.” (If you read Carr over the years, you know the reality was a lot closer to “A Clockwork Orange.”) That Carr didn’t meet the fate of Victor Riesel or Don Bolles was something of a miracle, considering the fact the law enforcement community, from the FBI on down, was Bulger-controlled. Political corruption in Massachusetts is eternal, of course, but thanks to Howie Carr, at least the state is no longer openly controlled by gangsters.

Climate of Fear: Jim Risen v. the Obama administration
The Obama DOJ’s effort to force New York Times investigative journalist Jim Risen to testify in a whistleblower prosecution and reveal his source is really remarkable and revealing in several ways; it should be receiving much more attention than it is. On its own, the whistleblower prosecution and accompanying targeting of Risen are pernicious, but more importantly, it underscores the menacing attempt by the Obama administration — as Risen yesterday pointed out — to threaten and intimidate whistleblowers, journalists and activists who meaningfully challenge what the government does in secret….http://www.salon.com/news/opinion/glenn_greenwald/2011/06/23/risen/index.html

I have to laugh at those stating that Wall Street guys are worse than the corrupt Bulgers. Making a bad business decision is not a crime. The Bulgers were part of the corrupt Irish way of life in Boston. If Bulger were still doing his “thing” in Boston for the last 16 years, the Russian Mafia would have wiped him out in a heart beat.

The Wall Street guys are worse than the Winter Hill Gang. The Winter Hill gang maybe had some Boston pols and cops in their pocket but the Wall Street gang has all of Washington DC in their pocket. They’ve corrupted our political system, shipped our union manufacturing jobs overseas, sank our economy and our dollar and transferred the great wealth of this nation from the vast middle class to a small corporate elite. These are the biggest thieves around and just like Putin sent several oligarchs to prisons in Siberia we should send these Wall Street types to work camps in Alaska where they can break rocks on the frozen tundra.

I read a while back that Dana White, head of the UFC, was driven out of South Boston by the mob who were shaking him down when he was a boxing trainer. Between the mob and the nanny state here, it’s hard to imagine UFC could have happened in Beantown but it would have been awesome to have all that stuff here instead of Vegas. There are a bunch of fighters out of here though.

Don’t people ever tire of blaming the Banksters when they were just the street arm of our crooked government. The strong arm tactics forcing the banks to give out liar loans were the direct results of a bogus redlining report that was manufactured by the MIT/Harvard idiots and the Boston Federal Reserve. Mass-Hole has become the California of the east coast!

As someone who grew up in Boston,not far from Southie, I knew that there were three ways to succeed in Boston, none of them particularly honest.

First, cultivate the largely Irish, but not entirely, political establishment. As this article shows, favors become bribes. Bribes generate jobs for the payors, and political support for the machine.

Second, associate with the Bulger type mob. There’s one in every Massachusetts community east of Worcester. And I include the tony Essex and Middlesex suburbs where many former Boston mobsters-Italian, Jewish and Irish, have relocated to invest their wealth and integrate their kids into patrician New England.

Third, secure a PhD, and curry favor with anyone associated with Harvard. Eventually you’ll find a sinecure at that surprisingly, for an alleged elite school, large bureaucracy. Academic or intellectual honesty not required.

Whitey Bulger is no less, nor more, than any of those in the above categories.